In vivo localization and identification of the antiplasmodial alkaloid dioncophylline A in the tropical liana Triphyophyllum peltatum by a combination of fluorescence, near infrared Fourier transform Raman microscopy, and density functional theory calculations
- 1 February 2006
- journal article
- biomedical systems-and-microorganisms
- Published by Wiley in Biopolymers
- Vol. 82 (4) , 295-300
- https://doi.org/10.1002/bip.20459
Abstract
Near infrared Fourier transform (NIR FT) micro Raman spectroscopy in combination with density functional theory (DFT) calculations has been applied for an in vivo localization of the antiplasmodial naphthylisoquinoline alkaloid dioncophylline A (1) in the tropical liana Triphyophyllum peltatum. Fluorescence microscopy images suggest finding this active agent in 10 μm big inclusions located in the cortex of the stem or the beginning of the leaves. By means of spatially resolved FT Raman micro spectroscopy, we could detect dioncophylline A (1) in these inclusions. FT Raman spectroscopy is an extremely selective tool capable of differentiating between various structurally similar naphthylisoquinoline alkaloids. With the help of DFT calculations, we succeeded in assigning the differences found in the FT Raman spectra of the various naphthylisoquinolines to νCC vibrations of the naphthyl ring. The presented results are of relevance for the investigation and extraction of new antimalarial active agents. © 2006 Wiley Periodicals, Inc. Biopolymers 82: 295–300, 2006 This article was originally published online as an accepted preprint. The “Published Online” date corresponds to the preprint version. You can request a copy of the preprint by emailing the Biopolymers editorial office at biopolymers@wiley.comKeywords
This publication has 15 references indexed in Scilit:
- The application of a SERS fiber probe for the investigation of sensitive biological samplesThe Analyst, 2004
- 3D QSAR Investigations on Antimalarial Naphthylisoquinoline Alkaloids by Comparative Molecular Similarity Indices Analysis (CoMSIA), Based on Different Alignment ApproachesJournal of Chemical Information and Computer Sciences, 2003
- Raman Spectroscopy—A Prospective Tool in the Life SciencesChemphyschem, 2002
- Invited review Bisquinoline antimalarials: their role in malaria chemotherapyInternational Journal for Parasitology, 1999
- In vitro inhibition of liver forms of the rodent malaria parasite Plasmodium berghei by naphthylisoquinoline alkaloids - structure-activity relationships of dioncophyllines A and C and ancistrocladineZeitschrift Fur Parasitenkunde-Parasitology Research, 1997
- The calculation of accurate harmonic frequencies of large molecules: the polycyclic aromatic hydrocarbons, a case studySpectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 1997
- The absolute stereostructure of dioncophylline a by anomalous X-ray dispersion of a 5-bromo derivativePhytochemistry, 1997
- Dioncophylline C from the roots of Triphyophyllum peltatum, the first 5,1′-coupled dioncophyllaceae alkaloidPhytochemistry, 1992
- Dioncopeltine A and dioncolactone A: Alkaloids from Triphyophyllum peltatumPhytochemistry, 1991
- On the structure of the dioncophyllaceae alkaloids dioncophylline a (“triphyophylline”) and “O-Methyl-Triphyophylline”Tetrahedron Letters, 1990